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Issue 6, 2004
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From a spin-off to the advantageous use in Diels–Alder reactions: a combined synthetic, spectroscopic and computational approach to N-(dienyl)acylamines

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Abstract

The acid-catalyzed condensation of aldehydes and acetamide has been shown to provide a pool of diverse equilibrating species. For the first time, the synthesis of substituted 1-N-acylamino-1,3-butadienes has been accomplished directly in moderate yields upon telomerization of two molecules of aldehyde with one molecule of carboxamide. Detailed spectroscopic and computational investigations establish the favourable formation of all-trans aminodienes under the reaction conditions. Employment thereof as diene building blocks in Diels–Alder reactions allows for the synthesis of carbocyclic molecules with high stereocontrol.

Graphical abstract: From a spin-off to the advantageous use in Diels–Alder reactions: a combined synthetic, spectroscopic and computational approach to N-(dienyl)acylamines

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Publication details

The article was received on 10 Dec 2003, accepted on 14 Jan 2004 and first published on 16 Feb 2004


Article type: Paper
DOI: 10.1039/B316026B
Citation: Org. Biomol. Chem., 2004,2, 845-851
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    From a spin-off to the advantageous use in Diels–Alder reactions: a combined synthetic, spectroscopic and computational approach to N-(dienyl)acylamines

    D. Gördes, A. J. V. Wangelin, S. Klaus, H. Neumann, D. Strübing, S. Hübner, H. Jiao, W. Baumann and M. Beller, Org. Biomol. Chem., 2004, 2, 845
    DOI: 10.1039/B316026B

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